#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:03:23 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180329 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/43/7154351.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7154351
loop_
_publ_author_name
'Baumann, Marcus'
'Rodriguez Garcia, Antonio M.'
'Baxendale, Ian R.'
_publ_section_title
;
 Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis
 of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4231
_journal_page_last               4239
_journal_paper_doi               10.1039/c5ob00245a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C10 H8 I N3 O4'
_chemical_formula_sum            'C10 H8 I N3 O4'
_chemical_formula_weight         361.09
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4957)
;
_audit_update_record
;
2014-12-15 deposited with the CCDC.
2015-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.424(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7611(3)
_cell_length_b                   4.6408(3)
_cell_length_c                   17.1279(3)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.54
_cell_measurement_theta_min      2.74
_cell_volume                     1173.29(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17049
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.38
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1660 before and 0.0832 after correction.
The Ratio of minimum to maximum transmission is 0.5916.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.044
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.010
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                3039
_reflns_number_total             3436
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00245a3.cif
_cod_data_source_block           14srv265
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3086 2015-02-26 13:12:21Z robertas 

 Adding full bibliography for 7154349--7154352.cif.
;
_cod_database_code               7154351
#BEGIN Tags that were not found in dictionaries:
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags_posn
I1 I 0.800365(10) 0.16103(3) 0.424289(8) 0.01398(7) Uani 1 d .
O1 O 0.93764(12) -0.5247(4) 0.73543(10) 0.0147(3) Uani 1 d .
O2 O 1.01070(13) -0.6134(4) 0.62787(11) 0.0172(4) Uani 1 d .
O3 O 0.62538(12) 0.5043(4) 0.80143(10) 0.0149(3) Uani 1 d .
O4 O 0.61259(13) 0.6868(4) 0.68008(12) 0.0174(4) Uani 1 d .
N1 N 0.75622(14) 0.1378(4) 0.75964(12) 0.0108(4) Uani 1 d .
N2 N 0.84241(13) -0.0865(4) 0.66205(11) 0.0091(4) Uani 1 d .
N3 N 0.95442(13) -0.4776(4) 0.66595(11) 0.0113(4) Uani 1 d .
C1 C 0.90584(16) -0.2610(5) 0.62628(14) 0.0110(4) Uani 1 d .
C2 C 0.90487(17) -0.2100(5) 0.54680(15) 0.0124(5) Uani 1 d .
H2 H 0.9419 -0.3021 0.5092 0.015 Uiso 1 calc R
C3 C 0.84005(16) 0.0001(5) 0.53180(13) 0.0123(4) Uani 1 d .
C4 C 0.80161(16) 0.0780(5) 0.60298(14) 0.0110(4) Uani 1 d .
C5 C 0.73523(16) 0.2790(5) 0.62538(14) 0.0114(4) Uani 1 d .
H5 H 0.7053 0.3955 0.5876 0.014 Uiso 1 calc R
C6 C 0.71509(16) 0.3018(5) 0.70256(14) 0.0105(4) Uani 1 d .
C7 C 0.81813(16) -0.0459(5) 0.73905(13) 0.0108(4) Uani 1 d .
H7 H 0.8478 -0.1562 0.7784 0.013 Uiso 1 calc R
C8 C 0.64556(15) 0.5197(5) 0.72599(14) 0.0122(4) Uani 1 d .
C9 C 0.55953(19) 0.7163(6) 0.82816(17) 0.0198(5) Uani 1 d .
H9A H 0.5025 0.6985 0.7977 0.024 Uiso 1 calc R
H9B H 0.5836 0.9135 0.8210 0.024 Uiso 1 calc R
C10 C 0.5421(3) 0.6614(7) 0.91236(19) 0.0324(8) Uani 1 d .
H10A H 0.5207 0.4630 0.9191 0.049 Uiso 1 calc GR
H10B H 0.4958 0.7956 0.9310 0.049 Uiso 1 calc GR
H10C H 0.5982 0.6893 0.9423 0.049 Uiso 1 calc GR
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01814(10) 0.01713(10) 0.00669(9) 0.00119(5) 0.00000(6) 0.00015(6)
O1 0.0179(8) 0.0159(9) 0.0103(8) 0.0019(7) 0.0012(6) 0.0005(7)
O2 0.0161(9) 0.0205(9) 0.0151(9) -0.0012(7) 0.0039(7) 0.0073(7)
O3 0.0154(8) 0.0169(9) 0.0125(8) -0.0007(7) 0.0043(6) 0.0047(7)
O4 0.0179(9) 0.0189(10) 0.0154(9) 0.0017(7) 0.0010(7) 0.0045(7)
N1 0.0122(9) 0.0124(10) 0.0079(9) -0.0006(7) -0.0007(7) -0.0011(7)
N2 0.0093(9) 0.0096(9) 0.0084(9) -0.0001(7) 0.0004(7) -0.0013(7)
N3 0.0099(9) 0.0120(9) 0.0121(9) -0.0012(8) -0.0002(7) -0.0017(7)
C1 0.0131(11) 0.0096(10) 0.0103(11) -0.0014(9) 0.0014(9) -0.0009(9)
C2 0.0139(11) 0.0121(11) 0.0113(11) -0.0017(8) 0.0022(9) -0.0009(9)
C3 0.0156(11) 0.0134(11) 0.0079(10) 0.0003(9) 0.0001(8) -0.0028(9)
C4 0.0129(10) 0.0126(10) 0.0075(10) 0.0006(8) -0.0002(8) -0.0026(9)
C5 0.0107(10) 0.0118(11) 0.0116(11) 0.0012(9) -0.0015(8) -0.0002(9)
C6 0.0093(10) 0.0118(11) 0.0105(11) -0.0013(8) -0.0002(8) -0.0024(8)
C7 0.0124(10) 0.0130(11) 0.0069(10) -0.0005(8) 0.0010(8) -0.0018(9)
C8 0.0093(10) 0.0119(11) 0.0153(11) -0.0014(9) 0.0007(8) -0.0025(9)
C9 0.0201(13) 0.0213(13) 0.0179(13) -0.0017(10) 0.0050(10) 0.0079(11)
C10 0.0354(18) 0.042(2) 0.0199(15) -0.0022(12) 0.0083(13) 0.0182(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 O3 C9 115.04(19)
C7 N1 C6 118.5(2)
C1 N2 C4 106.73(19)
C7 N2 C1 133.1(2)
C7 N2 C4 120.1(2)
O1 N3 C1 119.08(19)
O2 N3 O1 124.0(2)
O2 N3 C1 116.9(2)
N2 C1 N3 123.2(2)
C2 C1 N2 109.5(2)
C2 C1 N3 126.9(2)
C1 C2 H2 126.1
C1 C2 C3 107.7(2)
C3 C2 H2 126.1
C2 C3 I1 127.48(18)
C2 C3 C4 107.7(2)
C4 C3 I1 124.74(18)
N2 C4 C5 117.4(2)
C3 C4 N2 108.3(2)
C3 C4 C5 134.2(2)
C4 C5 H5 120.9
C6 C5 C4 118.3(2)
C6 C5 H5 120.9
N1 C6 C8 118.8(2)
C5 C6 N1 123.3(2)
C5 C6 C8 117.9(2)
N1 C7 N2 122.4(2)
N1 C7 H7 118.8
N2 C7 H7 118.8
O3 C8 C6 112.5(2)
O4 C8 O3 125.2(2)
O4 C8 C6 122.3(2)
O3 C9 H9A 110.1
O3 C9 H9B 110.1
O3 C9 C10 108.0(2)
H9A C9 H9B 108.4
C10 C9 H9A 110.1
C10 C9 H9B 110.1
C9 C10 H10A 109.5
C9 C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C3 2.068(2)
O1 N3 1.237(2)
O2 N3 1.233(3)
O3 C8 1.330(3)
O3 C9 1.459(3)
O4 C8 1.205(3)
N1 C6 1.377(3)
N1 C7 1.300(3)
N2 C1 1.384(3)
N2 C4 1.400(3)
N2 C7 1.382(3)
N3 C1 1.407(3)
C1 C2 1.382(3)
C2 H2 0.9500
C2 C3 1.389(3)
C3 C4 1.396(3)
C4 C5 1.408(3)
C5 H5 0.9500
C5 C6 1.361(3)
C6 C8 1.498(3)
C7 H7 0.9500
C9 H9A 0.9900
C9 H9B 0.9900
C9 C10 1.489(4)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C6 C8 O3 -6.7(3)
N1 C6 C8 O4 173.6(2)
N2 C1 N3 O1 3.1(3)
N2 C1 N3 O2 -178.2(2)
C2 C1 N3 O1 -168.8(2)
C2 C1 N3 O2 9.9(4)
C5 C6 C8 O3 174.1(2)
C5 C6 C8 O4 -5.6(4)
C6 C8 O3 C9 178.6(2)
C9 O3 C8 O4 -1.7(4)
C10 C9 O3 C8 177.7(2)
